new england road trip

This is a bit like asking "I am driving from London to York; what should I see?"

I don't mean to be rude, but we could be most helpful if we knew your interests, your budget, and the amount of time you have to spend. You could do hill walking, serious climbing, day sailing, multi-day sailing in a windjammer (large sailing vessel) shopping for jewelry and clothing, riding historic trains, sitting on a pier eating lobster and drinking beer, and a great deal more. What you are not likely to be able to do is swim or fish in the sea, though you can go out with a lobsterman to pull a few traps.

There are two major routes up the coast: I-95, a motorway just like all other motorways, that will get you there quickly and boringly or a series of coastal roads that will take you there in a much longer time but which may well be much more interesting. The coast of Maine is highly indented. The hillwalking and climbing would take you away from the coast and into New Hampshire, but you can see the highest peak in NH from Portland in Maine, so nothing is all that far.

yes I see your point Ackislander. we would enjoy things like horse riding, bear watching, sitting on a pier eating lobster!! I suppose you could say the gentle things!! we have 2 weeks and budget isnt really an issue as we want to make the most of our trip regardless of price, although we are not royalty!!!! the coastal road sounds great. we would also like to visit Vermont and salem. Is New York state worth a visit?? the mountains look amazing! Thanks for your help

Two weeks for a half-day drive! Cool!

Here are some ideas. Note that September is a busy tourist season and you'll want to book your lodging early. Some places will have 3 night minimums during this time.

After Boston: 2-3 nights Cape Ann (with a day trip to Salem. Cape Ann (Gloucester, Rockport) has a working fisherman's ports, sandy beaches (too cold to swim, though), an artist colony (lots of shoppes_, and nice views from cliffs.

4 nights Burlington area (maybe one night on the way, if you want to break up the drive). Drive northwest through the hills and small villages to visit Burlington, a beautiful small city on the side of a big lake. Take the ferry across the lake for a driving tour of the Adirondaks (New York) -- See Lake Placid, Saranac Lake, Au Sable, etc. Look for bears.

3 nights White Mountains/ Lake Winnepesauke area. Stay in Conway, Madison, or Meridith, maybe. Hike in the hills, take a boat tour on the lake, shop in the shops.

3 nights Coastal. Say in Portsmouth NH, or Portland, ME, or somewhere in between. Walk the town centers, enjoy the views, drive the coastal highways, eat lobster right off the boat, take a day-trip or longer cruise (check out Maine Windjammer cruises).

Last night, one of the small harbor towns on the way to Bar Harbor.

on the north shore area (Massachusetts shore north of Boston) you will definitely find good lobster, good beaches (we like Crane's Beach) and good scenery. Newburyport, a bit farther north, has Plum Island and some impressive sea captains' mansions.

In Maine Freeport is the home of L.L. Bean and lots of other outlet stores

In New York the Adirondack park area is beautiful, but with only 2 weeks I would stick to New England and explore more of the White Mts (New Hampshire) and Green Mts (Vermont).

I'd also suggest seeing some of New Hampshire, and tour around the Meredith area. You could see Old Man of the Mountain, (ok some of his face fell off not long ago, but he's still there) Indian Head, The Flume, and Lake Winnepasaukee and Lake Waukeewand. There are some lovely shops in the area and LOTS of outlet shopping not far away. September you should also see some colour starting or farther up in Maine, LOTS of colour. The Inn at Meredith is a nice place to stay right on the lake so the scenery is really beautiful. There are boat tours of the lake that you might want to do as well.

capxxx means Burlington VT on Lake Champlain. It's a nice college town, fun downtown and you can go further north just about into Canada and then drive down the Hero Islands ending up back in Burlington in time for lunch.
Agree to skip NY state because there is so much else to see.
Agree on visiting NH's White Mountains and the Lake Winnipesaukee area. Meredith and Wolfboro are lovely towns. The mountains would be an easy day trip and don't miss Center Sandwich area/Squam Lakes because it's so beautiful. Twice we have seen black bears near the road in this area. Drive the back roads.
So-called outlet shopping in Tilton NH (south of Meredith) and North Conway NH (before you head to Maine) - no sales tax in NH. From Wolfeboro it's probably 1 1/2 hours to Portland Maine. Take Rt 95 for a quick trip as far north as Brunswick. Then you can get off on Rt 1 and travel thru places like Wiscasset, Camden, etc. Just about every town on the Maine coast is worth seeing. Third weekend in Sept is usually the Common Ground Fair sponsored by the organic farmers association. This is not like any other country fair. Very nice handcrafts. I haven't been in several years but you might see some interesting domestic animals. Get out on the water, maybe a cruise out of Portsmouth NH on your return to Boston.
I've lived in NH about 50 years and this year finally saw my first NH moose (in my own yard). There are areas north of the White Mountains where you are almost guaranteed to see moose (google Moose Alley). We can have some wonderful weather in Sept. Much of the area is scenic although we have our favorites like picnicking on top of Mt Battie overlooking Camden Harbor or walking out to Owls Head Light near Rockland. There are scenic drives recommended on Yankee Magazine's website.
Recently visited with two other couples who are more familiar with areas of the White Mountains than we are. There are places we still need to see!

So, we have turned your trip up the coast of Maine into a tour of New England! All good advice here, but we have left you to sort it out. If you like driving through gentle mountain/hill country, you can go to Burlington. If you like higher, more rugged mountains combined with endless shopping in North Conway, the White Mountains await. Or you could stick strictly to the coast -- Salem, Gloucester, Cape Ann and Newburyport in Massachusetts, Portsmouth in New Hampshire, Ogunquit, Kennebunkport, Portland, Brunswick, Wiscasset, Boothbay Harbor, Camden, Rockland, and perhaps Monhegan Island in Maine. All will repay visits and study, and you will see why those of us who live in New England never want to leave.

The OP did say in a second post that they would also like to visit Vt and Salem and asked about NY state and the Adirondack Mts, so I think people have been responsive to these interests.

If the trip will go into very late September, there could be some good fall foliage by then in the Northeast Kingdom of Vt. Not around Burlington until later.

There really isn;t any plce for "bear watching". You may see one in many places (quite a few turn up in backyards in suburban New Jersey and I nearly hit one sitting in the middle of an off-ramp of Rte 8- about 30 minutes outside NYC. (But it was a young one and confued.)

You might see one almost anywhere that isn't mobbed with people and has some source of food. Just don't go anywhere near one - especially a mother with a cub - they can move VERY fast and are extemely large wild animals - often with little fear of humans.

when you get to Bar Harbor consider spending some time - an afternoon - on the Schoodic Pennisula. Its a beautiful quiet part of Acadia National Park and well worth the drive or ferry ride. Much less crowded and the scenery is amazing.

You might want to consider taking a 2- to 6-day windjammer cruise along Maine's midcoast...it's a great way to enjoy a lot of Maine's special features in one fell swoop: lobster bake, lighthouses, American maritime history, deserted islands, fishing villages, great sailing and food, seals and eagles, etc. There are 12 windjammers that operate out of Camden and Rockland, two great towns to explore. For details: www.sailmainecoast.com. Good luck with your planning!